Ethyl Bromide → HCID 178510893, compound

Participants

Reaction Steps

2-cyanoethanethioamide (300 mg, 3.00 mmol) and bromoethane (261 μL, 3.50 mmol) were added to an ethanolic solution of sodium ethoxide (3.50 mmol, 2.5 mL). The resulting mixture was stirred for 6 hours, 2-amino-6-chlorobenzoic acid (500 mg, 2.91 mmol) was added, and the reaction was refluxed overnight with stirring. A solid precipitate formed upon cooling of the reaction mixture, which was recovered by vacuum filtration and washed sequentially with ethanol, water, ethanol, and diethyl ether. The solid was then dried to yield 2-(5-chloro-4-oxo-1,4-dihydroquinazolin-2-yl)acetonitrile (148 mg, 22%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.15 (s, 2H), 7.54 (dd, J1=7.8 Hz, J2=1.1 Hz, 1H), 7.61 (dd, J1=8.2 Hz, J2=1.1 Hz, 1H), 7.74 (t, J=8.0 Hz, 1H).

Provenance & Evidence